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The same all-inclusive week in Mexico or the Dominican Republic can cost twice as much depending on the dates you pick. For Canadians, two things drive winter prices more than anything else: school holidays and how far ahead you book. Here is how to time your sun vacation to pay less.

The most expensive weeks to travel

  • Christmas and New Year: from about December 20 to January 3, demand from families and holiday travellers pushes prices to their highest level of the year.
  • March break: every province has a school break in March, but not on the same week. Ontario, Quebec, the Atlantic provinces and Western Canada are spread over several weeks, which means high prices for most of March.
  • Family Day and Presidents’ Day long weekends in February also add a bump.
  • Easter can be busy too, depending on the year.

The cheapest weeks to go south

  • Early December (before about December 18): the weather is already great, schools are still in session and resorts are hungry for guests. This is one of the best values of the season.
  • The first three weeks of January (after the holidays): everyone is back at work, credit cards are full, and tour operators drop prices to fill flights.
  • Late April and early May: once March break and Easter are over, prices fall again while the Caribbean is still dry and sunny.
  • Mid-week departures: leaving on a Tuesday or Wednesday is often cheaper than a Saturday or Sunday.

How far ahead should you book?

There is no magic date, but these rules of thumb work well for Canadians:

  • Christmas and March break: book early, ideally in late summer or early fall. The cheap rooms and family suites disappear first, and last-minute deals for these weeks are rare.
  • January and February off-peak weeks: booking one to three months ahead usually gives a good balance of choice and price.
  • Flexible travellers: last-minute deals (one to three weeks before departure) do exist in quiet weeks, but you have less choice of resort and room type.

For more ideas on short-notice trips, read our guide to last-minute hotel deals.

Price drops: book flexible, then check again

Many hotels and some packages offer free cancellation until a few days or weeks before arrival. Booking a refundable rate early protects you against price increases, and if the price drops later you can cancel and rebook. Read the cancellation rules carefully: package deals with flights often have stricter conditions than hotel-only bookings.

Package or separate bookings?

For Mexico and the Caribbean, flight and hotel packages from Canada are often cheaper than booking each separately, because tour operators and travel sites negotiate bulk rates. For destinations like Florida, Arizona or Costa Rica, where you may want a rental car and several hotels, separate bookings can be more flexible. The only way to know is to compare both for your exact dates.

Other ways to save

  • Check nearby airports: Hamilton, Ottawa, Québec City and other smaller airports sometimes have cheaper charter flights than Toronto Pearson or Montréal-Trudeau.
  • Travel for 6 or 8 nights instead of 7: odd durations can fall into cheaper flight rotations.
  • Use member prices: signing in to a travel site such as Expedia can unlock lower hotel rates.
  • Watch the Canadian dollar: prices for US destinations are often in US dollars, so the exchange rate matters for Florida and Arizona.

Quick summary

Best value: early December, the weeks after New Year’s, and late April. Most expensive: Christmas, March break and long weekends. Book peak weeks early, book off-peak weeks one to three months ahead, and always prefer refundable rates when you can.

Ready to see prices for your dates? Compare flights, hotels and packages on Expedia or use the search box below.

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